Deals on vacations and trips to Middlebury

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Middlebury flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Sunset Dunes Vacation Villas

Sunset Dunes Vacation Villas

3 out of 5
Price was $422, price is now $409 per person
$409
per person
Nov 13 - Nov 15
found 24 hours ago
Roundtrip flight included
Denver (DEN) to South Bend (SBN)
This villa features laundry facilities. Take advantage of the free self parking.
Morris Inn

Morris Inn

4 out of 5
Price was $1,041, price is now $939 per person
$939
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Tampa (TPA) to South Bend (SBN)
This hotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. Self parking, a business center, and a terrace are also offered.
Doubletree Hotel South Bend

Doubletree Hotel South Bend

4 out of 5
Downtown South Bend
Price was $471, price is now $464 per person
$464
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Tampa (TPA) to South Bend (SBN)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free WiFi and a free airport shuttle. You'll appreciate the free area shuttle, self parking, and 24-hour business center.

Top Middlebury hotels deals

Essenhaus Inn & Conference Center

Essenhaus Inn & Conference Center

3.5 out of 5
240 Hwy 20 Middlebury IN
$101 nightly
The price is $113 total per night
$113 total
Oct 11 - Oct 12
Total with taxes and fees
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like continental breakfast and free self parking.
Hampton Inn & Suites Middlebury

Hampton Inn & Suites Middlebury

2.5 out of 5
105 Crystal Heights Blvd Middlebury IN
Free Cancellation
Reserve now, pay when you stay
$112 nightly
The price is $126 total per night
$126 total
Oct 17 - Oct 18
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Enjoy the hot tub and free perks like buffet breakfast and free self parking. A 24-hour business center, free WiFi in public areas, and a snack bar/deli are also on offer.
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

Middlebury IN
$176 nightly
The price is $188 total per night
$188 total
Oct 11 - Oct 12
Total with taxes and fees
A garden is available at this cottage.
Van Buren Hotel

Van Buren Hotel

4 out of 5
1175 Van Buren Street Shipshewana IN
$90 nightly
The price is $103 total per night
$103 total
Oct 25 - Oct 26
Total with taxes and fees
This hotel features an indoor pool and a gym. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A terrace, a lobby fireplace, and a computer station are also on offer.
Farmstead Inn & Conference Center

Farmstead Inn & Conference Center

2.5 out of 5
370 S Van Buren St Shipshewana IN
$146 nightly
The price is $168 total per night
$168 total
Nov 1 - Nov 2
Total with taxes and fees
This hotel features an indoor pool and a gym. There's fun for all ages with a children's pool and a playground, and families will appreciate the picnic area. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking.
Blue Gate Garden Inn

Blue Gate Garden Inn

2.5 out of 5
800 South Van Buren Street Shipshewana IN
Free Cancellation
Reserve now, pay when you stay
$120 nightly
The price is $138 total per night
$138 total
Oct 11 - Oct 12
Total with taxes and fees
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Enjoy the hot tub and free perks like buffet breakfast and free self parking. Free WiFi in public areas, a terrace, and laundry facilities are also on offer.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Middlebury attractions

Stone Lake

Commune with nature and explore the great outdoors at Stone Lake during your travels in Middlebury. While in this family-friendly area, you can enjoy the restaurants.
See properties

Frequently asked questions

How much are vacation packages to Middlebury?
With deals starting at just $409, hotel and flight packages are a superb way to stretch your travel budget. Watch out Middlebury — here you come!
How long should my Middlebury vacation be?
Most sightseers vacation in Middlebury for approximately 2 nights. That being said, travel is all about discovering hidden gems and losing yourself in the moment — why not book a few extra nights so you can do just that?
Where can I get the best vacation package deals for Middlebury?
With at least 400 airline partners and 1,000,000 properties across the globe, it's hard to top Travelocity. Browse our comprehensive range and pick up the best Middlebury package deal. Isn't it amazing when planning a trip is that easy?
Why should I book my Middlebury vacation package with Travelocity?
Travel is all about making fantastic new memories and leaving all your worries behind — which is why we provide you with a professional team of customer service experts available 24/7 should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best price available on our terrific range of vacation packages. So what are you waiting for? There's no time like the present to secure the vacation you've always dreamed of.
Will I save money on my Middlebury car rental if I combine it with hotels and flights?
With a Middlebury vacation package, you can bundle your flight, hotel and car bookings and save a whole lot. If you're eager to uncover the best of this fantastic destination, why not start with Wrigley Field? This well-known attraction is 100 mi from Middlebury. With your own wheels, you'll be there in a flash.
Which airport is best for Middlebury?
There's a very good chance you'll land at South Bend Intl. Airport (SBN), situated 30 mi west of downtown Middlebury. Fort Wayne Intl. Airport (FWA) (55 mi away from central Middlebury) and Kalamazoo-Battle Creek Intl. Airport (AZO) (40 mi away from central Middlebury) are other choices.
What is there to do in Middlebury?
Deutsch Kase Haus should be toward the top of your travel itinerary. After you've crossed off this leading attraction, simply stroll the streets of Middlebury and find out what makes this vibrant place tick.
Where should I stay when visiting Middlebury?
If you're searching for someplace comfortable to lay your head, have a look at the Hampton Inn & Suites Middlebury. It's the top choice for many travelers.

Photos of local treasures

Browse Middlebury vacation photos for more inspiration

A log cabin with red shutters and a small porch.
A horse-drawn carriage with a covered wagon, parked on a dirt path with grass and trees in the background.
A black carriage with two horses tied to it, parked on a street.
A row of empty boats docked by a calm river, surrounded by trees with autumn foliage.
A Dutch County building with a covered walkway and red wagon wheels.